The Last Mission

Richard Holbrooke’s plan to avoid the mistakes of Vietnam in Afghanistan.

Special Representative Holbrooke, in New York.Credit Photograph by Brigitte Lacombe

A week after being elected President, Barack Obama summoned Richard Holbrooke to his transition headquarters, at the Hilton Hotel in Chicago. To some members of Obama’s staff, the invitation was surprising: Obama and Holbrooke hardly knew each other, and Holbrooke had firmly supported Hillary Clinton during the primaries. Although Holbrooke, a State Department veteran, had been careful not to disparage Obama, the President-elect’s advisers saw him as a problematic, if rare, talent. Holbrooke had a reputation for creating drama—speaking ill of rivals in government, hotly pursuing the press—and it was not clear that he could play unselfishly on the fanatically disciplined Obama team. In June, 2008, after Clinton dropped out of the race, Holbrooke began working his connections to the Obama campaign so aggressively that several friends warned him to tone it down. Holbrooke had important links to the new Administration, but his enemies nearly outnumbered his friends. What’s more, in the view of several White House aides, Holbrooke epitomized something that Obama had run against: a Democratic foreign-policy establishment that had supported the invasion of Iraq more on political grounds than on substantive ones, and that had spent years warding off Republican attacks on its lack of “toughness” instead of devising a national-security strategy that recognized the limits of American power.

Holbrooke, who is sixty-eight, had served under every Democratic President since John F. Kennedy, and Obama was familiar with his record, which extended from the Vietnam War, in the sixties, to the Balkan conflicts of the nineties; during the final eighteen months of Bill Clinton’s Presidency, Holbrooke served as Ambassador to the United Nations. In the past two decades, whenever a Democrat was poised to take the White House, a sideshow has centered on Holbrooke’s potential place in a new Administration. On several occasions, the position of Secretary of State—which he has coveted practically since he joined the foreign service, in 1962—has narrowly eluded him. In 1996, Hillary Clinton urged her husband to name the first female Secretary of State, and Madeleine Albright got the job over Holbrooke, who had recently led negotiations ending the war in Bosnia. Strobe Talbott, the president of the Brookings Institution, who served as Deputy Secretary of State under Bill Clinton, told me that, in 2000, “if Al Gore had been allowed to assume the Presidency, I believe Holbrooke would have been his Secretary of State.” In 2004, Holbrooke was reportedly on John Kerry’s short list. “It’s a brass ring that he kept grasping for and missing,” Talbott said.

This time, Holbrooke was never in the running. In Chicago, he spoke with the President-elect for nearly an hour. He left with the sense that he would not be excluded from serving in what could be the last Democratic Presidency of his professional life. But Obama already knew that he wanted Hillary Clinton as his Secretary of State. The choice softened the blow; she was Holbrooke’s ally, and her power far exceeded that of all competitors. An Obama adviser said, “It was the one Secretary of State he could accept with peace in his heart, because it was just a wholly different species of person.”

Obama, meanwhile, had decided that Holbrooke should take on the hardest foreign-policy problem that the Administration faced: Afghanistan and Pakistan. Related insurgencies threatened both governments; Al Qaeda had regrouped in the mountains along the border between the countries; in Afghanistan, American troops were bogged down in a war that was rapidly deteriorating.

Holbrooke had made trips to Afghanistan as a private citizen, in 2006 and 2008, travelling around the country, talking to Afghans from different backgrounds. He had written op-eds in the Washington Post proposing changes in American policy. The eradication of poppy fields in southern Afghanistan had alienated Afghan farmers and barely reduced heroin trafficking; Holbrooke argued that the U.S. should focus instead on apprehending high-level drug dealers, including those with ties to the government of President Hamid Karzai. The Bush Administration had given nearly unconditional support to Karzai, under whom “officially sanctioned corruption and the drug trade” had revitalized the Taliban. Holbrooke also recommended more development aid for the new democratic government in Pakistan, especially in the tribal regions, which had turned into a sanctuary for jihadists while the Bush Administration accepted the assurances of Pervez Musharraf, the country’s President at the time, that he was fighting extremism. Afghanistan and Pakistan now constituted a single theatre of war, Holbrooke wrote, where America would have an unavoidable interest long after the war in Iraq was history. “The conflict in Afghanistan will be far more costly and much, much longer than Americans realize,” he wrote in March, 2008. “This war, already in its seventh year, will eventually become the longest in American history.”

The Obama adviser said, “There’s almost an inevitability or gravitational force that pulls Holbrooke into relevant circles, because he makes himself indispensable.” A few days after being selected Secretary of State, Hillary Clinton called Holbrooke to offer him the job. In late November, they talked for three hours at Essex House, in New York. He already had a detailed conception of the new position. For starters, he would not be a “special envoy”—the title given to George Mitchell, Obama’s chief negotiator for the Middle East. “I’ve done that,” Holbrooke told me. (Under Bill Clinton, he had been a special envoy for both Cyprus and Kosovo.) “ ‘Envoy’ is an elegant diplomatic word. . . . I have nothing against it. It’s an honored and treasured word. It means envoi—you’re sent to do things. I was given a different task.” He wanted to be a “special representative.” The difference was more than semantic: in addition to being an emissary to the region, Holbrooke would run operations on the civilian side of American policy. He would create a rump regional bureau within the State Department, carved out of the Bureau of South and Central Asia, whose Afghanistan and Pakistan desks would report directly to him. He would assemble outside experts and officials from various government agencies to work for him, and he would report to the President through Hillary Clinton. Clinton told Holbrooke that he would be the civilian counterpart to General David Petraeus, the military head of Central Command. “I laughed,” Holbrooke told me. “I said, ‘He has more airplanes than I have telephones.’ “

When Holbrooke was in his mid-thirties, he had been the youngest ever Assistant Secretary of State, for East Asia, under Jimmy Carter. Two decades later, in his mid-fifties, he had served as Bill Clinton’s Assistant Secretary for Europe. Now, another decade on, he was to be a de-facto Assistant Secretary again—he described himself to me as “a junior, non-Cabinet-level official.” Holbrooke’s career appeared to be charting one of the longest plateaus in the history of the foreign service. In fact he took the mandate from Obama and Clinton and defined his role in a way that has made it unprecedented in American diplomacy.

According to several sources, Holbrooke thought that India and Iran, which played essential roles in the regional conflict, should also be part of his portfolio. (Holbrooke denies this.) But Iran was taken away by the White House, which appointed Dennis Ross to be the special adviser on the nuclear issue and other matters, and India was taken away by the Indians, who refused to be included in an office set up for fragile states beset with Islamist insurgencies. Obama had mentioned the conflict in Kashmir twice in the weeks after the election, and the government in New Delhi “went berserk,” according to someone familiar with the situation. Holbrooke later turned the setback into a quip: he was going to get through his new job without ever uttering the “K-word.”

Other than an airplane of his own, Holbrooke got everything he wanted. He was in charge of “Af-Pak”—a phrase that he used to make the point that the two countries could not be dealt with separately, as the Bush Administration had done, and that the war in Afghanistan could be resolved only by addressing the complex problems of Pakistan. Obama had been elected, in part, on a commitment to get America out of Iraq, and on a promise to show the world a less pugnacious face. But he had also stated his intention to intensify the war effort in Afghanistan, because Al Qaeda and the Taliban had reconstituted themselves. “Af-Pak’s tricky for him,” a senior Administration official said of Obama. “He’s always prided himself on being aware of the limits of American power and on knowing how to use it pragmatically. But he’s also pragmatic enough to see that this is the main threat.” When asked if Af-Pak was the biggest foreign-policy gamble of Obama’s Presidency, the official said, “Oh, yes. And he’s aware of that.” So the odd problem out was also the most important one, and for guidance the youthful new President had turned to one of the last icons of an earlier era, in which American greatness was assumed, the country’s diplomacy had expansive ambitions, and its foreign policy was dominated by a few men—among them Clark Clifford, Maxwell Taylor, Averell Harriman, and Dean Rusk, all of whom had been Holbrooke’s patrons.

On January 22nd, when Hillary Clinton announced Holbrooke’s appointment at the State Department, Holbrooke spotted John Negroponte in the audience. They had become friends in 1964, when both were doing diplomatic work in Saigon. In his remarks, Holbrooke mentioned their Vietnam connection. “I hope we will produce a better outcome this time,” he said with a smile. That day, he received a congratulatory e-mail from the first boss he ever had, Rufus Phillips, who for several years was in charge of civilian counter-insurgency in South Vietnam. Holbrooke answered the e-mail in one sentence: “It’s worse than the Nam!”

Holbrooke is a big man with a small head, and his frame is dominated by a square-shouldered trunk perched on long, thin legs. Friends he made in his twenties say that his character was fully formed by then. Leslie Gelb, the former Times columnist, was an aide to Senator Jacob Javits, of New York, when he met Holbrooke, in 1966. “He walked into the front office and asked to see the Senator,” Gelb said. “I think he was twelve years old at the time.” (Holbrooke was twenty-five, and working at the White House.) “In fact, he insisted on speaking to the Senator, but they shovelled him off to me, much to his expressed consternation. He wanted to talk to Javits about his views of Vietnam, of which he had many.”

In pictures from his high-school yearbook and from his years in Vietnam, Holbrooke is almost always smiling behind the thick black frames of his glasses. His features remain deceptively mild, as does his voice, which applies pressure with the quiet relentlessness of an underwater current. Holbrooke has been known to yell (during the negotiations over Bosnia, he browbeat the Serbian dictator, Slobodan Milosevic), but his usual strategy, in the manner of Lyndon Johnson, is to deploy cajolery, flattery, criticism, analysis, implied threat, teasing humor, fibs—any means at his disposal—to exert his will on a counterpart. Usually, he prevails.

“I wouldn’t call it conversation,” Gelb said. “It’s this sort of breathless monologue that you can only engage by interrupting. Dick is an advocate. He almost always has a case to make.” Holbrooke’s forcefulness is tempered by an endearing vulnerability—the nakedness of his ambitions and pleasures and insecurities. He takes pains arranging the seating chart for official dinners. Between government jobs, he worked as an investment banker, and, according to USA Today, he’s worth at least seventeen million dollars, but he still looks as if he’d dressed in a hurry. He reads voraciously, writes quickly and well, and consumes large quantities of schlock entertainment. (Holbrooke is especially fond of “There’s Something About Mary.”) His great advantage over most colleagues and opponents is his analytic and synthetic prowess, which allows him, for example, to break down the reasons for the Taliban’s successful propaganda campaign in the tribal areas while connecting it to imperial British history in the region. As for his flaws, he seems remarkably unaware of them. Holbrooke cannot be kidded about the trait for which he’s best known: his ego.

The notion that Holbrooke craves attention, which he bitterly resents and constantly feeds, is accurate but misleading. Far from undermining those he works for, Holbrooke is a loyal servant to power, with an old-fashioned respect for the Presidency. Once he took the new job, the restlessness and anxiety about his place in the order of things subsided, his energy found its proper outlet, and he bore down, in Strobe Talbott’s words, like “a precision-guided munition.”

Holbrooke, in turn, inspires great loyalty. Christopher Hill, the American Ambassador in Baghdad, who worked under Holbrooke during the Bosnia negotiations, said, “If you have enemies—and he does—you also need friends, and he has a lot.” The Obama Administration is crowded with officials in their thirties and forties who are former Holbrooke protégés, and though they acknowledge that he could be brutal with his staff, they still regard the experience as a high point of their careers; they were given serious responsibilities and made to feel that they were part of something historic. Holbrooke’s relationships with his seniors and subordinates are less turbulent than those with his peers, such as James Dobbins, who followed Holbrooke as special envoy to the Balkans, and who found himself in constant conflict with his predecessor. “It’s the flip side of his good side,” Talbott said. “If you’re not on the team and you’re in his way, God help you.”

A close friend of Holbrooke’s joked, “If I paid attention to some of the specific things he did, I would have murdered him.” The friend said of Holbrooke’s aggressiveness, “He doesn’t even know he’s doing it, and that’s why he didn’t become Secretary of State. But, in terms of talent, it is far in excess of what you see around you.”

Gahl Burt, a former aide to Henry Kissinger, met Holbrooke at the State Department in the seventies and remains a close friend. She said, “I know people dislike Dick Holbrooke. There are people who won’t sit in the same room with him. But what I love about him is he has a heart.” She mentioned work that he had done on AIDS prevention and refugee assistance. “He’s irrepressible, which makes him successful with a Slobodan Milosevic,” Burt said. “Richard is a bully with a heart. And people know it and admire it, and so they put up with the bullying.”

In August, 2008, at a writers’ conference in Sun Valley, Idaho, Holbrooke shared a stage with Shashi Tharoor, the Indian diplomat, who lost out to Ban Ki-moon in the competition to succeed Kofi Annan as Secretary-General of the United Nations. The topic—the future of the U.N.—could not have been more anodyne, and Tharoor’s opening remarks made the familiar point that the Security Council is outmoded and needs to be enlarged. Almost instinctively, as if he needed to shatter the polite mood and dominate the stage, Holbrooke systematically exposed the conflicting national interests that would arise, until Tharoor’s suggestion had been demolished. Tharoor mustered a diplomatic smile as Holbrooke concluded, “In thirty years, there will be a committee still studying the issue, and you, Shashi, will be on it.”

Next to Holbrooke’s desk in his office, on the first floor of the State Department, hangs a black-and-white photograph of him as a young man, walking in the sun-saturated Mekong Delta next to Ambassador Maxwell Taylor and several Vietnamese officials. Although Holbrooke made his international reputation by negotiating peace in Bosnia, his professional life was shaped in Vietnam. “I lived, ate, and slept Vietnam,” Holbrooke wrote in an unpublished 1992 essay. “At times, I thought I knew more about it than almost anyone else—certainly more than anyone higher-ranking than me in the U.S. government.” Holbrooke’s experience with Vietnam foreshadowed, in uncanny ways, his latest and, he insists, final mission.

Holbrooke had originally wanted to be a journalist. He was the sports editor of his high-school paper, in Scarsdale, New York, and then, at Brown University, he edited the Daily Herald. But James Reston, the Washington bureau chief of the Times, declined to hire him straight out of college. For Holbrooke, it was the Times or nothing, and he abandoned his journalistic ambitions. Yet he always befriended reporters who covered the international conflicts in which he was involved, taking an acute interest in their work and relationships, offering unsolicited advice on how to write their stories, and sometimes identifying more with them than with his staid official colleagues. “He loved reporters,” Frank G. Wisner, a retired ambassador and a close friend of Holbrooke, said. “He had an instinct what to feed reporters, what to deny them—how you used your access to the reportorial class to advance your own bureaucratic agenda.” A State Department official said, “At his very core, he’s a frustrated foreign correspondent. He thinks like a journalist, he’s dogged like a journalist—he’ll go to the source instead of just getting canned briefings. He thinks in narratives.”

At Scarsdale High School, Holbrooke’s best friend and fellow-editor was David Rusk, a son of Dean Rusk. In 1957, when Holbrooke was fifteen, his father, a doctor, died, and he grew closer to the Rusk family. The next year, Dean Rusk spoke at the high school about the foreign service—the first Holbrooke had heard of it. Then came the bright optimism of the New Frontier, with President Kennedy’s stirring call to “ask not,” and Rusk became Secretary of State. “I’m a product of the Kennedy era,” Holbrooke said. “Kennedy’s Inaugural plus the accident of Dean Rusk brought me into the government. Those were my values.”

Holbrooke was barely twenty-one when he entered the foreign service, in 1962. The next year, he arrived in South Vietnam, just as the U.S. was being pulled deeper into the political chaos of a guerrilla war. Because he was a bachelor, Holbrooke was assigned to a post outside Saigon, as the top American civilian in a poor province in the Lower Mekong Delta called Ba Xuyen. He lived alone above a shop, took showers from a cistern, and went out to the U.S. airbase five or six nights a week to watch whatever movie happened to be showing. (He saw “Seven Brides for Seven Brothers” a dozen times.) “The terrible truth that people do not like to admit was that the war was fun for young men, at least it was fun if they were civilians or journalists,” Holbrooke later wrote. “I was at the center of the world, right where I wanted to be. I had wanted to see war, like Stephen Crane, and I had wanted to participate in history, and I was doing both.”

In Ba Xuyen, Holbrooke distributed cement, cooking oil, and roofing thatch to villagers, built schools, helped train and arm the militias of the local strategic hamlets, and wrangled with the disagreeable Vietnamese province chief. The term of that era for this kind of wartime aid effort was “pacification”; today it’s “nation-building,” and it reflects the idea that, in a counter-insurgency, the main battle is for the allegiance of the population. “Changing hearts and minds—all the smart young men thought that,” Gelb recalled. “That became sort of a telltale belief of my generation.” Four decades later, after strategic bungling in Iraq and Afghanistan, the smart young men discovered it again.

Holbrooke arrived in Vietnam in 1963, and worked on the pacification effort in the Lower Mekong Delta.

Holbrooke didn’t question the need to fight Communism in South Vietnam. But, he said, because he was stationed in the countryside, where the war was being fought, he realized early on that “we weren’t being honest with ourselves. . . . I saw the credibility gap.” The pessimistic dispatches of David Halberstam and other journalists depicted the war more accurately than the memos and cables passing through official channels. In 1964, Holbrooke became a staff assistant at the U.S. Embassy in Saigon. (“Richard is hardly the sort who’s going to get isolated in a provincial assignment,” Wisner said.) Holbrooke shared his contrary views with his superiors, including Ambassador Henry Cabot Lodge, Jr. On a flight back to Saigon from the field with Lodge, he argued that the tactic of creating “free-fire zones,” in which anything that moved could be killed, only embittered the Vietnamese and created more Vietcong. Holbrooke successfully mixed candor and careerism, rising through the Embassy’s hierarchy by seeking out powerful patrons, impressing them with his intelligence, and making no secret of his critical viewpoint (while concealing the disdain he felt for a few of them).

In 1966, Holbrooke was called back to Washington and placed under a special assistant to President Lyndon Johnson, Robert Komer, whose office was taking control of all the pacification programs in Vietnam. Komer was such a brutal bureaucratic fighter that Lodge nicknamed him the Blowtorch. Holbrooke, whose nickname later became the Bulldozer, grew even more brash. After a trip to South Vietnam in late 1966, Holbrooke wrote Komer a memo, reporting, “I have never seen the Americans in such disarray.”

Komer’s new office represented a turn toward more intelligent counter-insurgency, and it helped check the Vietcong’s recruiting efforts; but it came late, and it was undermined by the American strategy of big-unit ground combat, and by the hollowness of the South Vietnamese government. Anthony Lake, the diplomat, was Holbrooke’s colleague and close friend in those years. (Their friendship, always competitive, eventually curdled.) Lake said that pacification had backfired by “focussing on programs at the expense of local politics”: “The more we did with the programs, the more we were undercutting the credibility and even legitimacy of the Saigon government.”

Holbrooke began losing faith in the war. He told me, “The most senior people in the U.S. government—the best and the brightest, if you will—were deluding themselves.” In early 1967, Nicholas Katzenbach, Rusk’s deputy at the State Department, hired Holbrooke. “I was a sucker for Richard,” Katzenbach, who is now eighty-seven, told me. “He never had any hesitation in giving his own opinion, which I think he regarded as superior to yours.” Every Thursday afternoon, Katzenbach convened senior officials for an informal discussion of Vietnam. Because the meeting had no official status and produced no paper trail—the point was a candid conversation, over drinks—Katzenbach called the gathering the Non-Group. Holbrooke was desperate to attend. “He pestered me, to the point I couldn’t stand it any longer,” Katzenbach said. At the Non-Group, Holbrooke met leading figures of the establishment—Ambassador Averell Harriman; Secretary of Defense Robert McNamara; his deputy, Cyrus Vance—all of whom became his benefactors.

In November, 1967, Holbrooke drafted a remarkable seventeen-page memo to President Johnson, over Katzenbach’s name. Without quite saying that the United States should withdraw, he argued that Hanoi was winning, not on the battlefield but in America:

Hanoi uses time the way the Russians used terrain before Napoleon’s advance on Moscow, always retreating, losing every battle, but eventually creating conditions in which the enemy can no longer function. For Napoleon it was his long supply lines and the cold Russian winter; Hanoi hopes that for us it will be the mounting dissension, impatience, and frustration caused by a protracted war without fronts or other visible signs of success; a growing need to choose between guns and butter; and an increasing American repugnance at finding, for the first time, their own country cast as “the heavy.”

Johnson had two choices. He could escalate the war in an attempt to strike a decisive blow against North Vietnam—an unlikely outcome. Or he could accept the impossibility of defeating the Communists in South Vietnam, and try instead to reduce civilian casualties, turn over more responsibility for fighting to the Vietnamese, pressure the government in Saigon to improve its performance, and seek an opening for negotiations. Holbrooke showed the memo to Katzenbach. “I was very reluctant to send it, because I knew Johnson would go up in smoke,” Katzenbach said. “But I agreed with it, and so I sent it to Johnson.” The President never acknowledged the memo.

In 1968, Holbrooke joined the American delegation at the peace talks with the North Vietnamese in Paris. “Holbrooke wants to always talk with the other side,” Katzenbach said. “He always thinks there’s some negotiation, some middle road. He always thinks he’ll learn more than he’ll give away.” But the talks made no progress, and after the election of Richard Nixon that November, Holbrooke decamped to Princeton, becoming a fellow at the Woodrow Wilson School. He soon wrote Anthony Lake, who had joined the new Administration, with a detailed proposal for a ceasefire, American withdrawal, and power-sharing between Saigon and the Vietcong. “In any case, it is your problem again and not mine anymore,” Holbrooke signed off, though he remained “always ready to tell you why the latest plan won’t work.”

Vietnam didn’t haunt Holbrooke with lifelong self-reproach: he was too young to be crippled by the burden of responsibility, and a bias for action leaves the strain of tragedy out of his character. “He understands where he went awry in Vietnam, but he doesn’t dwell on past errors,” Gelb said. “He’s looking for the next thing to do.” Unlike other Democrats of the Vietnam era, Holbrooke did not rethink the fundamental role of American power and leadership in the world. “I’m informed by Vietnam,” Holbrooke told me. “I’m not imprisoned by it.”

In 1970, he became the Peace Corps director in Morocco. The next year, he visited Peace Corps operations in Afghanistan. The country left a lasting impression. He later said, “I saw this romantic, exotic, harmonious, multi-ethnic society, just a few years before it was destroyed.”

While running for President, Obama promised to shift America’s focus from Iraq to the region where the September 11th attacks had actually been planned. This policy had enough merit to go almost uncontested during the campaign, but Obama’s position was also inflected with political calculations. Morton Abramowitz, a veteran of the foreign-policy establishment, put it bluntly: “Obama, in a fit of absent-mindedness, to show he was tough, made Afghanistan his signature issue because he wanted to get out of Iraq. And this is going to be God-damned difficult.” Within weeks of taking office, Obama decided to approve the deployment to Afghanistan of seventeen thousand additional troops and four thousand trainers. He did so without having time to come up with a strategy for how they should be used. Meanwhile, the Taliban had taken control of a dozen districts in Afghanistan.

Bruce Riedel, a retired C.I.A. officer, told me that in January, on a trip to Afghanistan, Vice-President-elect Joe Biden discovered that U.S. policy was in disarray. When he asked why American troops were there, no two people gave him the same answer. Shortly after the Inauguration, Obama went to the Pentagon, where the Joint Chiefs of Staff gave a slide briefing; instead of delineating a clear goal, the briefing listed more than a dozen goals. Obama called Riedel and asked him to lead a two-month strategic review of the war. Holbrooke would work closely with him.

Riedel had studied the region for years, but the most recent intelligence gave new grounds for worry. “Al Qaeda is recruiting and training individuals with Western European passports in their camps in Pakistan,” he said. “There’s only one reason they’re doing that”—attacks on the West. “They don’t need guys with British and French passports to attack the Marriott Hotel in Islamabad.” The Taliban leadership—the Quetta shura, led by Mullah Omar—not only still existed (though the Pakistanis denied it) but was meeting at the same time as Riedel’s group. “They were doing their strategic review, probably with a lot less bureaucracy,” Riedel said.

At the Eisenhower Executive Office Building, in Washington, the review group looked at an array of options, including an abandonment of counter-insurgency in Afghanistan and a very narrow focus on Al Qaeda. This “minimalist” view has been embraced by a diverse group of thinkers, including Rory Stewart, the British diplomat and writer, who runs a foundation in Kabul; the conservative columnist George F. Will; and Leslie Gelb, whose recent book, “Power Rules,” argues for a reduced American commitment in Afghanistan, and recommends, among other things, threatening air strikes in order to deter the Taliban from allowing Al Qaeda back into the country. In this view, it’s a dangerous illusion to think that America knows how to fight insurgents in the deserts and mountains of Afghanistan, and to believe that America can help build a viable Afghan state. Afghanistan is too tribal, too ancient, too recalcitrant to be shaped by foreigners; Americans, for their part, are ignorant of the complexities of foreign places and too entranced with their own ideas to understand whom they’re dealing with. Let Afghanistan follow its own destiny, the minimalists argue, and use American power—Predator drones, Special Forces units, spies—to contain Al Qaeda.

In the review group, the proponent of a scaled-back policy was Biden, who consistently voiced skepticism, asking: Is there an alternative? “Biden was very courageous,” Gelb, who knows him well, said. “It gave the Administration self-doubt.”

A pure counterterror approach had, in fact, been the Bush Administration’s policy for years: kill or capture terrorist leaders, with minimal support for political institutions in Kabul and Islamabad. It had created the mess that Obama inherited, with two countries under threat from insurgents and Al Qaeda’s strength increasing. “Al Qaeda doesn’t exist in a vacuum,” Riedel said. “They’re part of a syndicate of terrorist groups. Selective counterterrorism won’t get you anywhere, because the bad guys don’t stay in their lanes.” And without an extensive military presence and connections to the Pakistani and Afghan governments the U.S. would likely lose the intelligence networks that have been built up since 9/11. Obama would have to accept the risk that Al Qaeda might pull off another catastrophic attack. The abandonment of Afghanistan to the Taliban would also be a dire prospect for Afghans, especially women, but in war-weary America this argument no longer had force. The basis for a policy had to be American self-interest.

“Yes, living well is the best revenge, but right now I’d settle just for doing better than my brother-in-law.”

As the strategic review continued, through February and March, support for the war kept slipping. Democrats had generally considered Afghanistan to be the “good war,” as opposed to Iraq, but, once Obama was in office and the withdrawal from Iraq had begun, congressional leaders such as David Obey, of Wisconsin, announced that they would give the Administration twelve months to show progress in Afghanistan. This unrealistic time frame—which coincides with the run-up to the 2010 elections—was adopted by numerous Administration officials. By August, more than half of Americans, and seventy per cent of Democrats, had turned against the war. “ ‘Afghanistan is Vietnam and the graveyard of empires’—that chorus comes mainly from the President’s supporters,” Riedel said.

There were obvious similarities between Afghanistan and Vietnam: a rural insurgency, a weak and corrupt American ally, and an enemy sanctuary across the border. The differences were also worth noting: the Vietcong had a strong base of support in South Vietnam, while the Taliban were reviled across much of Afghanistan, and their popularity, confined to Pashtun areas, was based on tribal and ideological, not nationalistic, grounds. In the view of Holbrooke and the other members of Riedel’s group, one difference was paramount: Vietnam had never posed a direct threat to the United States, but the Taliban, because of its alliance with terrorist networks, did. This argument won the day, and it set the Obama Administration on a course of escalation that would be difficult to undo. But a shadow hovered: a prolonged war had once destroyed a Democratic Administration. As Riedel put it, “Johnson sort of slid into an escalatory ladder, without any strategy for measuring the results.”

On March 18th, Obama flew to Los Angeles, for an appearance on the “Tonight Show,” and Rahm Emanuel, his chief of staff, arranged for Riedel to travel with the President and summarize the review. Obama spent an hour talking with him. The senior Administration official said that, in the last phase of the strategy review, “the President asked by far the hardest questions: If this doesn’t work, then what?” Unlike Johnson, Obama wanted a serious internal debate about his policy, and he got one, with advisers considering whether the war was already lost. Yet the conclusion was, in a sense, foreordained by the President’s campaign promises. Intellectual honesty in the private councils of the White House told you something about the calibre of the officials involved, but in the realm of public policy it made little difference.

On March 27th, the Administration rolled out its new strategy for Afghanistan and Pakistan. Obama, in a speech, reminded the country that Al Qaeda was still trying to attack America. “I want the American people to understand that we have a clear and focussed goal: to disrupt, dismantle, and defeat Al Qaeda in Pakistan and Afghanistan,” he said. This rationale represented a return to basics, a dispensing with illusions about transforming other people’s societies. It sounded tough-minded, and it offered Americans a simple and self-interested reason for their young people to risk death in remote places. But the implications were broad. By the end of his speech, Obama had promised to support women’s rights, to send lawyers and agricultural experts to Afghanistan to reform its government and economy, and to offer seven and a half billion dollars in new aid for schools, roads, and democracy in Pakistan. He also said that the Administration would establish benchmarks for measuring progress. Last week, around fifty of them were finally released to Congress.

The new strategy meant different things to different audiences. According to Shuja Nawaz, an analyst of the Pakistani military, the aid package was seen in Pakistan as a sign of American support, while in Afghanistan the Obama strategy, with its talk of lowered expectations for Afghan democracy, raised fears of reduced commitment. On May 30th, Morton Abramowitz ran into Holbrooke at a memorial service. “There’s a long-term problem,” Abramowitz told him. “It’s going to take a lot of money, a lot of effort. And the Administration, in order to get the money, has to convey there’s a short-term fix. But there is no short-term fix.” John Kerry, the chairman of the Senate Committee on Foreign Relations, told me, “Everyone’s on a relatively short fuse here to see that the strategy is being defined correctly.” He expressed concern that the Administration’s strategy “demands greater nation-building resources than people may be aware and certainly than we have thus far committed.” James Dobbins, now with the RAND Corporation, couches the problem this way: “There is a gap between the reason we’re there and what we’re doing. The rationale is counterterrorism. The strategy is counter-insurgency.”

I asked Holbrooke about the conflicting thrusts of Obama’s speech. “Read it carefully,” he said. “The President put the stress on Al Qaeda because that’s the reason we’re there, and that’s the core difference between Iraq and Vietnam, on the one hand, and Afghanistan, on the other. But he never said anything about leaving Afghanistan on a specified timetable. Our goal has got to be to get combat troops out eventually. There’s only one way to do that, and that’s to build up Afghan capability, and get the Pakistanis to coöperate more. But any correct policy toward Afghanistan involves extended economic assistance.”

Holbrooke assembled his team in the idiosyncratic manner of the “Ocean’s Eleven” heist movies. In early December, 2008, Vali Nasr, an Iranian-American scholar of the Muslim world, especially Pakistan, received a text message from Holbrooke around midnight, wondering if Nasr was awake. When Nasr called back, Holbrooke told him that his new special-representative role was going to be mentioned in the Washington Post the next day. “I don’t want you to accept any job in the government without letting me make a counter-offer,” Holbrooke said. “Don’t tell anyone except your wife,” he told Nasr. Holbrooke also called Barnett Rubin, of New York University, perhaps the country’s leading expert on Afghanistan, who was in North Carolina, preparing to give a talk to the 82nd Airborne Division before it deployed. Holbrooke locked him in as well.

In early February, Steve Berk, an official with the Department of Agriculture, was reading the Times at his house, in Palm Beach County, Florida, when he noticed an article about Holbrooke’s new assignment, alongside a picture from 2006: Holbrooke and his wife, Kati Marton, an author and a human-rights activist, perched atop a rusting Soviet tank in the Afghan city of Herat. Berk, who had worked briefly in Afghanistan, wrote an e-mail to Holbrooke with some ideas for agriculture in Afghanistan, expecting no answer. Within a few days, he had an interview scheduled. Holbrooke, who knew little about agriculture other than that it was an essential but neglected area in Afghanistan, pummelled Berk with questions, then offered him a job. “I’m really proud of you,” Holbrooke later told him. “You did exactly what a government official should do—you barged in the door and found exactly the right person.”

One night in April, Holbrooke was on the last Delta shuttle from Washington to New York when Rina Amiri recognized him. An Afghan-American woman in her thirties, Amiri came from a royalist family in Kabul that had fled to America when the Afghan king Zahir Shah was overthrown, in 1973; since 2001, she had been working in Afghanistan on political and human-rights issues, for the U.N. and then the Open Society Institute. Amiri sat in the row behind Holbrooke and pressed him about a constitutional problem related to the Afghan elections. After a few minutes, Holbrooke suddenly said, “You know, I’m building this team.”

“I know,” Amiri said. “But I’m here to lobby you.”

“I’m very efficient. I just turned your lobbying into a job interview.” Holbrooke fixed her with a steady look. “Do you realize no one will offer you the type of opportunity I’m offering to affect your country?”

She asked him for more specifics. “You will have a lot of latitude,” he said. “That’s the way I work.”

Amiri was wary of losing her independence. She also worried about Holbrooke’s reputation for abrasiveness. Would she be in a meeting in Kabul where her American boss pounded his fist on the table? It took a month, but eventually Holbrooke won her over, hiring her as an Afghanistan expert. (Henry Kissinger once said, “If Richard calls you and asks you for something, just say yes. If you say no, you’ll eventually get to yes, but the journey will be very painful.”)

Holbrooke has taken over two suites of offices at State Department headquarters, filling them with a staff that has grown to some thirty people. (He had told Clinton that he would need around fifteen.) Nine government agencies, including the C.I.A., the F.B.I., the Defense and Treasury Departments, and two foreign countries, Britain and Canada, are represented in the office. The Af-Pak suites are treasuries of Holbrookeana: photographs of him with Bill Clinton and Kofi Annan, in East Timor; with George and Barbara Bush, in Washington; with Slobodan Milosevic and Warren Christopher, in Dayton. There is a large image of Holbrooke leaving a building in Sarajevo, alongside a guard with an automatic rifle; a framed op-ed eulogizing Dean Rusk; a letter from Richard Nixon; multiple copies of his book “To End a War.” These furnishings are both a monument to himself and an attempt to infuse the staff with a sense of historical purpose. Anyone who works for Holbrooke can walk into his office. When Petraeus visited, he said, “This is the flattest organization I’ve ever seen.” Members of the staff compare it to a startup company.

Vikram Singh, a young counter-insurgency expert who accompanied Holbrooke on a trip to the region and ended up working for him, said, “He is a tough boss. I rarely go home before nine or ten. You’ve got to be there and available all the time, and you have hell to pay when you’re not. He can be a pain, but he promotes his people.”

Holbrooke in Ghazni, Afghanistan, last July. He visits the region at least every other month.Photograph by Marco Di Lauro; Reportage by Getty Images

Young officials who had heard stories about Holbrooke’s temper and ego were surprised to find that he welcomed critical views, as long as they were well considered. He went out of his way to bring opposing viewpoints into his office. Barnett Rubin, a part-time adviser, kept his position at New York University, which allows him more flexibility than Holbrooke’s other aides. In his role as an academic, he can explore the possibility of negotiations with Taliban leaders, although official American policy is to reconcile only with insurgents who have already laid down their arms and accepted political participation. Rubin has written that even the best counter-insurgency cannot win the war. Instead, he argues, there should be an international effort to give Pakistan security guarantees; then its military could be encouraged to push Taliban leaders to make a deal with the Afghan government, thus giving America a way out. If Rubin serves as a kind of in-house dissident, Holbrooke’s other Afghanistan expert, Amiri, regards any deal that would lead to power-sharing with hard-line elements in the Taliban leadership as a betrayal of the Afghan people. Holbrooke wants both points of view on his staff.

“You have to test your hypothesis against other theories,” Holbrooke said. “Certainty in the face of complex situations is very dangerous.” During Vietnam, he had seen officials such as McGeorge Bundy, Kennedy’s and Johnson’s national-security adviser, “cut people to ribbons because the views they were getting weren’t acceptable.” Washington promotes tactical brilliance framed by strategic conformity—the facility to outmaneuver one’s counterpart in a discussion, without questioning fundamental assumptions. A more farsighted wisdom is often unwelcome. In 1975, with Bundy in mind, Holbrooke published an essay in Harper’s in which he wrote, “The smartest man in the room is not always right.” That was one of the lessons of Vietnam. Holbrooke described his method to me as “a form of democratic centralism, where you want open airing of views and opinions and suggestions upward, but once the policy’s decided you want rigorous, disciplined implementation of it. And very often in the government the exact opposite happens. People sit in a room, they don’t air their real differences, a false and sloppy consensus papers over those underlying differences, and they go back to their offices and continue to work at cross-purposes, even actively undermining each other.”

Holbrooke’s team was moving so fast that the National Security Council was months behind him in assembling its own offices related to Afghanistan and Pakistan. To keep the rest of the government informed, and to avoid turf battles, in June Holbrooke and Lieutenant General Doug Lute, the President’s adviser on Afghanistan and Pakistan, started a weekly Monday-evening meeting at the State Department for all the relevant agencies. Lute called it the “shura.” With Holbrooke at the helm, it had the freewheeling quality of Katzenbach’s Non-Group.

In addition to setting up his office, Holbrooke had a number of important relationships to nurture. There was Petraeus, whom he had not known until Hillary Clinton introduced them. There was Clinton herself, with whom he often spoke. (Clinton told me that the Administration was “coördinating our diplomatic and development and defense efforts much more closely than they were before.”) There was Congress. And there was the President, who wanted updates on Afghanistan and Pakistan every day.

Within a few weeks of Obama’s speech on the new policy, Pakistan’s condition suddenly slipped from worrying to alarming. Under Musharraf, the military had struck deals giving Islamist militants de-facto control over many of the semi-autonomous tribal areas along the Afghan border. In 2007, under the mantle of the Pakistani Taliban, the militants spread into the settled districts of the North-West Frontier Province, terrorizing residents of the Swat Valley—beheading policemen, shutting down girls’ schools—until Musharraf’s successor as President, the civilian Asif Zardari, agreed, in February, to give the Taliban control over Swat.

On April 21st, Taliban fighters in Swat began attacking government outposts in the neighboring district of Buner, which put them within an hour’s drive of Islamabad. The Pakistani government appeared to be paralyzed by the threat, and Washington was thrown into a panic. Most of the strategic review had been focussed on Afghanistan; Pakistan had been discussed mainly as a sanctuary for the Taliban and as a potential recipient of substantial aid. There was no detailed strategy for keeping the Pakistani state intact.

The next morning at the daily staff meeting, Holbrooke expressed concern about the Taliban incursions into Buner. It was Vali Nasr’s first day of work—security clearances are protracted matters in Washington—and Holbrooke asked for his opinion. “The Taliban are not going to march into Islamabad,” Nasr said. More worrisome was the Pakistani government’s decision to give up on Swat.

Holbrooke and his staff discussed the dire condition of the Pakistani state. It had great difficulty delivering services and was threatened by collapse from within: its civilian politicians sniping at each other, its government and military at odds. The Taliban was not going to take over Karachi and Lahore, but its advance might cause a chain reaction of violence and jihadism that could plunge Pakistan into chaos. The U.S. had to stiffen Pakistan’s will to fight the Taliban, and it had to help prevent the country from disintegrating. The feud between President Zardari and the opposition leader, Nawaz Sharif, needed to be resolved. The issue was governance, not just extremism.

After the meeting, Holbrooke told Nasr, “Write a memo.”

“By when?”

“Late tonight.” Holbrooke had a meeting scheduled for four the next afternoon with Obama and Clinton, at the White House. At 3:45 P.M., he gave copies of Nasr’s four-page memo to Clinton and Tom Donilon, the deputy national-security adviser, and Clinton read it while they were standing outside the Oval Office. When they went in, Clinton gave copies to Obama and other senior officials.

The President skimmed the memo. “I agree with Vali Nasr,” he said.

Holbrooke texted Nasr at midnight. “What a first day!” he wrote. There was a part of Holbrooke that stood aside from the events in which he was participating and saw them in their larger context, as if he were writing the drama with the aid of hindsight and historical analogy. (“He’s romantic about a lot of things,” Nicholas Katzenbach said. “That includes himself.”) Once, during a siege in Bosnia, when French peacekeepers were calling for more helicopters, Holbrooke told the journalist Joe Klein, “This is exactly like Dien Bien Phu!”—the site of the French defeat in Vietnam, in 1954. A few months ago, he mentioned to me a Times article about a Taliban ambush in a poppy field in southern Afghanistan and, recalling a notorious Vietcong victory in the Mekong Delta, exclaimed, “It’s just like Ap Bac!” He often urged his younger aides to remember everything, because nothing they did in the future would ever be this exciting. “One day, you’ll write about this,” he told Nasr. “I can’t promise you every day your memo will go to the President, but today it did.”

During the following months, Holbrooke spent a lot of time urging Nawaz Sharif to form a coalition government with Zardari. Along with Petraeus and Admiral Mike Mullen, the chairman of the Joint Chiefs of Staff, Holbrooke pressured General Ashfaq Kayani, the head of the Pakistani Army, to push back against the Taliban in Swat; in May, when the military’s operations displaced more than two million people from their homes, Holbrooke and Clinton procured several hundred million dollars in emergency aid. If the refugees were not able to return home soon and safely, Holbrooke believed, they could become another threat to Pakistan’s stability. In June, Holbrooke visited a sweltering camp in the flatlands south of Swat, and the event won praise from the ordinarily anti-American local media, which pointed out that no senior Pakistani leader had yet done the same.

One day in June, I sat down with Nasr in the State Department cafeteria. “Pakistan has become the eye of the storm, and I don’t think the American public understands this,” he said. Washington’s focus on terrorists in the border areas had neglected the deeper problem. The Pakistani military was now fighting the Pakistani Taliban in Swat, but it was still making distinctions among extremists—maintaining support for the Afghan Taliban and jihadist groups in Punjab. Underlying the crisis was an unhappy history with the United States: on the Pakistani side, a sense of being exploited for American strategic goals; on the American side, a sense of being chronically deceived.

“Richard gets it,” Nasr said. “He knows where we are with Pakistan is a symptom of twenty years of neglect. It’s a symptom of two countries that aren’t enemies but don’t trust each other.” Pakistan was counting on something that Hafez Assad, of Syria, once said: “America is short of breath.” Eventually, the Americans would leave Afghanistan, allowing Pakistan to pursue its own interests in the region. “Countries don’t change their strategic vision overnight,” Nasr told me. “It’s not as simple as Bush saying, ‘I hate terrorism, you hate terrorism, we’re all on the same page.’ This is a long, hard battle. We need to turn the Pakistani military, but we can’t do that without getting it to see its interests differently, which means building relations.”

In late July, I travelled with Holbrooke and a dozen members of his staff to Pakistan and Afghanistan. Holbrooke visits the region at least every other month; it requires repeated persuasion to bring the policies of two foreign governments that dislike each other into closer alignment with American interests. Holbrooke’s assignment, it was becoming clear, carried overlapping echoes from American history and from his own. He was running an interagency effort supporting a counter-insurgency, as his old boss Robert Komer had in Vietnam. He was mapping out a new vision for American interests in a volatile region, as his old friend Henry Kissinger had done in Southeast Asia. And he was positioning himself to be a mediator in an international conflict, as he had done in the Balkans. (Holbrooke might have sworn not to use the “K-word,” but he was going to India almost as often as he was going to the two other countries.) What I didn’t understand was how these roles came together, and, beyond that, what overarching strategy Holbrooke thought was required for him to succeed.

We flew in an Air National Guard 737; Holbrooke had his own curtained-off compartment. Somewhere over the Atlantic, he emerged barefoot in yellow pajamas and, doing knee bends in the aisle, held an informal staff meeting. He looked tired—he complained of exhaustion throughout the trip—and yet he hummed with energy. Holbrooke handed a memo to Vikram Singh. The memo, written by another aide, was a plan for transferring more authority from NATO’s provincial reconstruction teams to Afghans. “Just get it into an action-plan form,” Holbrooke said. “See my notes.”

“You want something for the President by Thursday?” Singh asked.

“I’m not sure,” Holbrooke said. “It’s a lovely work. But it doesn’t go far enough—develop this more.” He pointed at the memo, on which he had scribbled “NOT OFTEN ENOUGH!,” “NOT GOOD ENOUGH,” and “YES!” He said, “This part is bullshit—we’re not going to do it.” And “Change words like ‘sometimes,’ which means ‘never.’ “

The memo’s theme was one of Holbrooke’s obsessions: how to increase American involvement without reducing Afghan capacity. His answer was to channel resources through the Afghan ministries, rather than allowing aid money to be siphoned off by foreign contractors. Holbrooke was now vetting U.S. aid contracts for Afghanistan. But, in the absence of any meaningful government in most of Afghanistan’s provinces, there was always a temptation to do things faster and better by going around the Afghans. “ ‘The dependency track,’ “ he read aloud, explaining, “The more help they need, the more dependent they get for their help, and then it’s ‘Ah, let the Americans do that.’ In Vietnam that’s exactly what happened.”

The conversation turned to Pakistan. Holbrooke lamented the flight of educated Pakistanis to the United States. “That’s why Hillary’s big idea of tapping the diaspora is so important,” he said. Clinton had urged Pakistani-American doctors, especially women, to volunteer in the refugee areas. “We can’t do it for them.”

That week, an electricity crisis was sparking riots in Pakistan. “If you could turn the lights on a few more hours a day, it would increase public good will,” Nasr said.

“The first short story in the book I’m reading, the central figure is an electrician,” Holbrooke said. “I have to read you one paragraph from the beginning.” He retreated to his compartment and returned with a copy of “In Other Rooms, Other Wonders,” by the Pakistani writer Daniyal Mueenuddin. He read aloud from the first page, and then said, “I gave a copy to the President. I don’t know if he’s read it. It’s beautiful.”

Business got done, but mainly Holbrooke held forth, admitting his young staff into his store of knowledge. He had told me, “The people born in the late thirties and forties are pretty much running out of time.” He was talking about himself and his peers. “This group on the plane are emblematic of the next generation. They aren’t shaped by the Vietnam War, which is centrally important. They aren’t either informed or encumbered by it. Vietnam is as far away from them as World War I was from me. I’m afraid they’re going to come out of my office and say, ‘Oh, Jesus, more war stories from World War I.’ “ He went on, “The World War II generation believed the United States could do anything—anything. . . . And Vietnam was a shattering experience for everyone. But these guys weren’t even born, or they were in diapers. That was forty years ago. I really hate to talk about Vietnam. I don’t think about it every day.”

Later, I asked Singh if Vietnam came up often. “He’s not going to be trapped by his Vietnam ghosts,” Singh said. “But he’s going to think about the parallels in proactive, forward-thinking ways. And it’s incredibly powerful.”

Islamabad felt like a capital under siege. We were driven at night from the airport to a barricaded hotel in a convoy of S.U.V.s that wove in and out of single file in evasive maneuvers, along broad avenues that had been cleared in advance and were lined with soldiers and police. Holbrooke disappeared for hours into secretive talks in government offices, always emerging with the banal news that the talks had been “productive,” even when his aides told me that they had not.

One evening, we went to President House, a floodlit Bauhaus-style structure, which had been built by the military dictator Zia ul-Haq in the nineteen-eighties. The reception room was guarded by ceremonial soldiers standing at rigid attention in traditional turbans topped with fans of starched black cotton. After a few minutes, the President entered: a short, smiling, dumpy man with a thin mustache, in a dark-blue suit and a pink tie. As Holbrooke introduced Asif Zardari to his staff, the President kept making quips, like a nervous night-club comedian.

“You’ve lost weight,” he told Holbrooke. “What have you been doing?”

“All I do is work.”

“You were working in Italy? On the beaches?”

“I was in Italy,” Holbrooke admitted. “You’re very well informed.” He observed that, with each of his visits, Pakistan seemed to have improved a little more.

“It’s the karma,” Zardari said. “You bring good stars to us. We believe in that, we Eastern people.”

Allowed one question, I asked Zardari if Pakistan’s main security threat was the Taliban or India, and, if it was India, how Holbrooke could help if he couldn’t address Kashmir. Zardari gave a tortured answer that invoked the Great Game—the nineteenth-century contest between Britain and Russia for control of Central Asia—and midway through he lost the thread. “Maybe if we hadn’t been a buffer state we’d have escaped this security mind-set,” he concluded. “Ambassador Holbrooke can help us move from the extreme mind-set to a civilized discussion with the world.”

Later, Holbrooke told me, vaguely, that his meetings with other Pakistani leaders—especially those with General Ashfaq Kayani, the military chief, and General Ahmad Pasha, the head of Pakistan’s intelligence agency—had centered on “the refugees, and the strategic challenge of dealing with Afghanistan, whether they’re going to consolidate Swat or move on to Waziristan.” Pakistani operations in Waziristan, the heartland of the Taliban and Al Qaeda, were apparently on hold.

Holbrooke expressed satisfaction that the Pakistani military was finally taking on homegrown militants in Swat. But it wasn’t at all clear that the generals’ world view had changed. They still allowed the Afghan Taliban to use Pakistan as a sanctuary, apparently in the hope that the insurgents would counteract a growing Indian influence in Afghanistan. “The Pakistanis are scared that this is some kind of sandwich India wants to make of Pakistan,” Shuja Nawaz, the military analyst, said. “The Pakistanis don’t want an unfriendly Pashtun government in Kabul.” A Western diplomat who had spent most of the past decade in Kabul said that Pakistan’s military leaders “are actively engaged in the double game . . . enabling and facilitating a Taliban-led insurgency into Afghanistan.”

I asked Holbrooke if he ever got into disagreements with the Pakistanis about intelligence. “Sometimes they just flatly tell us we don’t have the right information,” he said. Even when he knew it was true? “Sometimes.” He thought for a moment. “The relationship with Pakistan is so fraught with a history of disappointment on both sides. . . . We can’t align our interests exactly, because they live in a different space, and their history is defined by their relationship with India. . . . The one thing I believe we can do with Pakistan is to try to reach a strategically symmetrical view on the danger posed by Al Qaeda and its allies. That’s the proximate strategic goal.”

I pointed out that Pakistan’s support for the Afghan Taliban suggested that even this goal would remain elusive. “Sometimes we part ways, sometimes we’re allied,” Holbrooke said. “It’s not so clear. This theory that they’re the sole sponsor of the Taliban is just as overstated as the theory that we have a total symmetry.” He added, “On the other hand, their own Army information chief said the other day they have continuing contacts.”

Shuja Nawaz said, “Richard Holbrooke can be a tough negotiator in a closed-door session with the Pakistanis and get a lot done. But if you do it in public the doors close.” Just before Holbrooke travelled to Pakistan in April, he and Mike Mullen publicly alluded to ties between Pakistani intelligence and the Afghan Taliban, and the generals reacted with extreme displeasure. Nawaz pronounced it “probably the worst-ever visit by an American team,” adding, “It was a complete disaster.” Since then, Holbrooke has been more careful, and some people in Kabul fear that he is in danger of becoming the latest American official to fall for Pakistani assurances. Saad Mohseni, the founder of Afghanistan’s largest media group, and a friend of Holbrooke’s, said, “I think he overestimates what he can do with the Pakistanis. The Pakistanis have played hardball with the best, and Holbrooke’s got his match there.”

In 1995, Christopher Hill spent months watching Holbrooke negotiate over Bosnia. “He keeps you off balance. He doesn’t show his cards. He makes you think you have to do the deal with him, but that he might not be able to sell it to the other side. He uses humor. He gets this dyspeptic look on his face so that they have to ask him, ‘What is it?,’ and he’ll say, ‘I’m worried. I don’t know if it’s going to work.’ He uses all these performance acts to achieve his goals.” In March, to coax Zardari into ending his feud with Sharif, Holbrooke warned that Congress might ignore the Administration’s pleas and refuse to increase aid. But that was as far as he could go. There was no deal to strike with the Pakistanis, only trust to build, and Holbrooke’s outsized personality seemed to be under wraps. In moments when I overheard him talking to Pakistani leaders, he took the solicitous tone of someone reassuring an unstable friend. “It’s like dealing with psychologically abused children,” a member of his staff said. “You don’t focus on the screaming and violence—you just hug them tighter.”

At a dinner party in Islamabad, I met a thirty-year-old businessman who told me that, as the head of a family with a huge following of religious mystics, he effectively controls up to eight hundred thousand votes. Beneath Pakistan’s dysfunctional government lies a social system that, in rural areas, remains feudal. The Taliban in Swat and the militant groups in Punjab have exploited the grievances of Pakistan’s rural poor, promising them land and justice. At an official reception in Islamabad, I chatted with an elegant young member of the Senate who had an Ivy League education, and who was being groomed as a diplomat; that day in her district, where her family was one of the largest landowners, her constituents were rioting and burning railroad cars because of the electricity shortage. At such moments, it’s tempting to think that if Pakistan were Russia the year would be 1910.

Part of Holbrooke’s mission in Islamabad was to talk to ordinary Pakistanis, to try to disinfect the air of growing anti-Americanism and convey a message of genuine concern. Holbrooke gave numerous interviews to local journalists and television anchors, providing blunt but not unfriendly answers to often hostile questions, and eventually winning a grudging respect. At the hotel, he had breakfast with a group of refugees who had fled to Islamabad from Swat. Among them were the owner of an anti-Taliban radio station, a women’s activist who had distributed a video of a young Pakistani woman being flogged by militants, and the director of a girls’ school that had been shut down by the Taliban. Some of Holbrooke’s guests expressed as much suspicion of the military—whose operations in Swat had destroyed livelihoods without killing any top Taliban leaders—as of the extremists. None of them thought it was safe to go home.

Holbrooke spent an intense hour listening to their stories and asking sympathetic questions. “I know it’s dangerous—good luck to you,” he told them at the end. “It’s very hard for me to give you easy answers.” He added, “We’re your friends, we’re your allies. What discourages me most is that so many Pakistanis think the United States is responsible for your problems.”

All along the Mall, one of Lahore’s main thoroughfares, stand monuments in red granite from the British Raj: the post office, a museum, administrative buildings, Punjab University. Since 9/11, America has spent $15.4 billion in Pakistan. Yet Ahmed Rashid, one of Pakistan’s leading journalists, told me, “There is not a single monument to American aid in Pakistan. There is not a school, there is not a hospital, there is not a road, there is not a dam, there is not a new seed, a new crop. There is not a single mark. Have you set up even one teachers’ training college for women? In my conversations with Holbrooke, I said, ‘You’ve got to leave monuments. You’ve got to do one or two really big things.’ “ Rashid suggested teacher training, agricultural research, and hydroelectric projects. He thought that Holbrooke was hungry for new ideas, and liked that he could “bang heads,” which was necessary in this part of the world. But, Rashid said, “Holbrooke had no idea what he’d walked into.”

In Islamabad, it became clear how few levers Holbrooke had at his disposal. Many of the subjects central to U.S.-Pakistan relations—drones, the Afghan Taliban, Kashmir—were off limits to public discussion. Even the seven and a half billion dollars in aid over five years that is awaiting approval by Congress falls far short of what Holbrooke once estimated as Pakistan’s actual need: fifty billion dollars. Because of Pakistan’s sensitivity about its sovereignty, he had been unable to persuade its military to allow American helicopters to bring aid to the refugees. Holbrooke hadn’t even been able to get the Pakistani military to help free the captured American journalist David Rohde, who, before escaping, in June, had been held by militants with connections to Pakistani intelligence. Fourteen years ago, when Rohde was taken prisoner by Serbian militiamen, in Bosnia, Holbrooke had made his release a condition of the Dayton talks, and Milosevic had complied.

Holbrooke was denied the tools required to hammer out a grand bargain for the region: for example, an agreement in which Pakistan stopped offering sanctuary to the Afghan Taliban in exchange for a deal with India over Kashmir. Instead, according to Vali Nasr, Holbrooke had to “claw his way up by addressing other issues,” such as the threat to Pakistan from homegrown extremism. He would have to try to change Pakistan’s perception of its own interests indirectly. Nasr called it “remote-control nation-building.”

When we flew over the Hindu Kush and landed in the mud-colored sprawl of Kabul, Holbrooke’s longtime chief of staff, Rosemarie Pauli, said, “It always reminds me of Sarajevo.” All around the airport were signs—uniforms, armored vehicles—of a heavy military presence. In Afghanistan, the atmosphere of the trip changed: Holbrooke switched his suit for a pink checked shirt, khakis, sunglasses, and a U.S.A.I.D. baseball cap, and he was greeted at each destination by American officers and civilian officials. He seemed less like a visiting emissary than like a proconsul inspecting a vast operation over which he commanded much of the authority.

For two days, we flew, by C-130 transport plane and Black Hawk helicopter, around the southern provinces, where an otherworldly heat rose from the desert and reports of intense fighting met us at every stop. The ruggedness of travel in Afghanistan and the proximity of the war energized Holbrooke. At briefings in each province, he asked questions that showed an astonishing grasp of detail.

In Helmand, American marines had just arrived, and they and British troops found themselves in bloody combat with Taliban cells. The provincial capital, Lashkar Gah, had been built with American assistance under Truman and Eisenhower, and we drove past a derelict movie theatre and an abandoned building that had once housed U.S.A.I.D. Holbrooke met with the governor, Gulab Mangal, and they discussed whether the price of this year’s wheat harvest would be high enough to dissuade farmers from planting poppies. Just before our arrival, British troops had found and burned a cache of three hundred tons of opium in Helmand. To Holbrooke, it proved the wisdom of the Administration’s policy of concentrating on drug dealers instead of crop eradication.

“Why do people join the Taliban?” Holbrooke asked Mangal. (It was a question that he asked everywhere he went.)

“Lack of knowledge, religious inspiration, lack of jobs, poverty,” the Governor said. “Others, because of our wrong practices. And a large number because of pressure—because they will be killed.”

“Do you have a program for those who want to leave the Taliban and come back to the government?”

The Governor said he had discussed the subject that morning with elders in one of the districts. “But will they get jobs?” Holbrooke pressed. “The last program didn’t work very well.”

The final stop on Holbrooke’s tour was Ghazni Province, south of Kabul. Polish battalions were stationed there, and, like other NATO allies in Helmand and Kandahar, the Poles found that support from the Afghan Army was woefully lacking; the police were barely present. Holbrooke, who had kept harping on the need to transfer responsibility to the Afghans, was appalled. “We can keep doing this for a while, but sooner or later we’ll turn it over to the Afghans,” he said. “I’ve seen this problem in many countries around the world, but I have never seen it at this level, outside of places like Angola and Kosovo.”

That day, Holbrooke and Karl Eikenberry, the U.S. Ambassador, met with the governor of Ghazni, Usman Usmani—a Karzai crony and an associate of the President’s brother, Ahmed Wali, who is believed to have got fabulously rich off the drug trade. Security in Ghazni had deteriorated sharply, but Usmani offered a portrait of the local insurgency which placed the blame entirely on Pakistanis, Chechens, and Arabs. Holbrooke didn’t bother to comment. Instead, he asked how many registered voters in the province would be unable to vote in the Presidential election, on August 20th, because of surging Taliban violence.

“Not more than one hundred thousand,” the Governor said. “Five or ten per cent.”

“There are one million people in Ghazni, right?” Holbrooke said. “Some of them are too young to vote. So it must be at least twenty per cent! It’s a lot more than ten per cent, Governor. We have to be honest with each other. Let’s deal with it, but let’s start with facts.”

The visit ended with a slide presentation on agriculture, by a colonel from the Texas National Guard. Holbrooke, who was planning to increase sixfold the number of agricultural advisers, stopped the colonel on a slide that showed a list of local projects. “Take No. 8, the Jaghatu Apiary Training Center,” Holbrooke said. “We all use this phrase ‘capacity-building.’ But, I can assure you, a year ago we were not doing capacity-building. Only ten per cent of our aid went through the government here.” The Texans’ projects aided local farmers, he pointed out, but they were entirely separate from the Afghan government. The minister of agriculture, Asif Rahimi, was present, and Holbrooke said to him, “Mr. Minister, we want the people of Ghazni to think of your government as the place where they can go for services. Much as we love the Texas National Guard, they’re not going to be here forever. Our goal here, under the new plan that Ambassador Eikenberry is overseeing, is to strengthen your government, not to do it ourselves. Otherwise”—he turned back to the colonel from Houston—“your apiary training will come and go like the wind. It’ll be a memory. Yesterday we were in Lashkar Gah, which in the fifties was known as Little America, with American schools, American movie theatres, streets laid out like an American suburb. All gone.”

In late May, I spent a few days with a U.S. Army unit in Wardak Province, southwest of Kabul. There had been rain, and the valleys between the brown mountains were green with apricot and apple orchards. Last year, Wardak—half an hour’s drive from the capital—had almost fallen under Taliban control, and the highway that connects Kabul to Kandahar had been all but shut down, with dozens of produce trucks burned. Seven drivers were beheaded. There had been only a hundred and fifty American soldiers in a province of half a million people. This past February, fifteen hundred soldiers, originally scheduled to deploy to Iraq, arrived in Wardak, five months ahead of the additional troops authorized by Obama. They set up combat outposts in each district, up the road from the village bazaars. By May, the highway had become secure, and farmers could transport their goods to Kabul. A number of villagers said that they felt safer than a year ago, but shadowy armed men continued to intimidate anyone coöperating with the government. “Seven years of unfulfilled promises,” an American battalion commander, Lieutenant Colonel Kimo Gallahue, said. “For the first time, we’re doing counter-insurgency here.” Another officer, Major Kit Parker, said, “If we can’t get Wardak right, nothing else is going to fly.”

The Americans in Wardak showed a sophistication about the fight which had come from repeated tours in Iraq and Afghanistan. Counter-insurgency, which just three years ago was discussed by a handful of dissident Army officers and outside experts, is now the lingua franca of American combat units. They talked about “population security” and “governance” and “economic development,” as if they were experts from an aid agency. They had learned enough to avoid using the term “Taliban,” which oversimplified an enemy composed of disparate elements, including more criminals and unemployed youths than Islamist ideologues.

But these lessons had come very late. Sarah Chayes, a former reporter who founded a sustainable-development coöperative in Kandahar, and who is now an adviser to General Stanley McChrystal, the American commander in Afghanistan, told me, “What the Afghans expected of us was to help create a decent government. Instead, we gave them warlords, because we were focussed on counterterrorism.” Zeroing in on killing the enemy, with grossly insufficient troops on the ground, had led directly to the overuse of air strikes and the killing of civilians.

Meanwhile, every time an Afghan encountered the government, he was hurt by it—abused, asked for a bribe, hauled off to jail without evidence. At least the Taliban offered justice; they heard disputes and delivered swift, if often brutal, verdicts, such as confinement in a box or death. As a result, the Taliban was regaining prestige. Insurgents collected taxes and even set up a commission to hear grievances against their fighters, something that neither the Afghan government nor NATO had done.

“The biggest complaint you hear from Afghan folks is there’s no connection to the government,” said Captain Jason Adler, a company commander in a district of Wardak called Sayed Abad, where there was still a fair amount of fighting. (The day I arrived at the combat outpost, the company was holding a memorial service for two sergeants who had just been killed in an ambush.) I walked down from the American base to the bazaar in the midday sun and sat with a dozen Afghan men gathered under a thatch shelter. Grievances began pouring out.

“If you go to government officials, they just put money in their pockets,” a watermelon seller said. “They have their properties in Dubai—they don’t care about the poor.”

A mechanic, in a long, greasy shirt, said, “Most of our police, they’re no good, they have drug problems. We want the police to take responsibility and bring peace for us. We don’t want police who are there to take money.” He got up to return to work. Most of the men under the shelter were jobless. These men had little affection for the Taliban, but they had almost no enthusiasm for the upcoming Presidential election, and no good words for any of the candidates, including President Karzai.

“Our government is all corrupt,” an old man in a turban said. “We need a system to give more money to the poor. When the Taliban were in power, there was peace, there wasn’t one gunshot at that time. They didn’t help the poor, but there was peace. The last eight years, we’ve had nothing.”

Holbrooke once told me that three things could cause America to lose the war: the Taliban sanctuary in Pakistan, civilian casualties, and corruption. The Afghan government was so crooked that NATO considered it as much of a threat to success as the Taliban. Members of Holbrooke’s team heard that, after the election, Karzai might replace Governor Mangal, who had a reputation for being clean. They heard that the former police chief of Helmand, a notorious drug dealer, was one of Karzai’s main fund-raisers. And they heard that Karzai’s aides sometimes intervened to release a detainee who had ties to Karzai’s brother. Holbrooke was debating how to raise such concerns when he met with Karzai, in Kabul, and I had the sense that he had not yet figured out his strategy.

Holbrooke’s op-eds in the Post had been critical of Karzai, and a former U.S. official familiar with Afghan politics described his manner at their meetings earlier this year as “imperial and directive.” Karzai had begun to fear that the new American Administration wanted to get rid of him—last year, during a lunch in Kabul, Joe Biden threw down his napkin and walked out—and he met Holbrooke’s pressure with defiance. “Holbrooke’s approach backfired,” the former official said. “He went out there and antagonized him first, without having a plan of how you would get rid of Karzai.”

Holbrooke had inherited a major problem: Afghanistan’s elections were constitutionally scheduled to take place between one and two months before Karzai’s term ended, on May 22nd. But the Afghan election commission had decided to delay them until August, in order to have more time to prepare. Who would be President in the interim? The Obama Administration, feeling that stability was paramount, believed that Karzai should stay in office. Holbrooke invoked the political chaos in South Vietnam that followed the 1963 overthrow of President Diem by an American-backed coup. The American political strategy in Afghanistan was essentially on hold until after the elections, and Holbrooke seemed disinclined to continue to press Karzai to reform his government.

A NATO official with a lot of experience in Afghanistan told me that Holbrooke’s day-to-day activities—so frantic that some Americans concluded he couldn’t possibly keep track of everything he was doing—were beside the point. The agriculture programs and the rest of it were “ancillary” to the main problem, which was the government of Afghanistan: “Nothing else matters if you don’t get this right.” The NATO official worried that Holbrooke, instead of leaning hard on the Karzai government, might see Karzai as a necessary conduit for cutting a deal with the Taliban that would allow the Americans to leave. “Holbrooke is fundamentally not a nation-builder, he’s a dealmaker,” the official said. “But this is not something you can bargain your way out of.”

Holbrooke, of course, had spent his youth trying to reform the government of South Vietnam and ended up seeking a negotiated solution. He had asked Ambassador Tim Carney, another Vietnam hand, to run the election-monitoring unit at the Embassy in Kabul. Over dinner and Scotch in the cafeteria, Carney told me, “You’ve got to go back to Vietnam, though this is not something Richard will say. He understands that we get into relationships that give the leaders of countries the strength of their weakness.” The corrupt rulers of countries where the U.S. is at war can simply dare the Americans to end their support. “We can collapse the whole thing, but that’s all we can do,” Carney said. “What other leverage do we have?”

Burt Field, an Air Force major general and Holbrooke’s military adviser, was beginning to question the military’s model of how to fight the Taliban. He said that the Americans were telling the Afghans, “We’re going to keep the Taliban off your back and connect you to your government—and that’s counter-insurgency.” But, Field went on, “it’s premised on the fact that the government wants to be able to provide those key services. What if the premise is false?”

In Kabul, Holbrooke and Karzai faced off over lunch at a long banquet table in the Presidential palace, each man flanked by his advisers. Karzai, dressed in a white tunic and a black jacket, acted theatrically, calling out to aides for information in a stage voice, then expressing shock when they predicted lower voter turnout because of violence in Pashtun areas, where he drew most of his support.

“You’re worried about the effect on the Pashtun people,” Holbrooke said.

“And the aftermath of the elections. The effect on Al Qaeda and the Taliban. We’ve done an analysis.”

Karzai’s intelligence chief, Amrullah Saleh, explained that low turnout would give the Taliban a propaganda victory. “That’s the main point,” Karzai cut in. “They will claim control of the people.”

“And the territory,” Saleh added.

“And the territory.”

Holbrooke sensed where this was leading, and he said, “Let’s be clear—the elections will take place on August 20th.” Karzai hastened to agree.

Holbrooke then chided him: “Wherever our troops have driven out the Taliban in Helmand over the last few weeks, there has been no effort to bring in administrative structures of your government.”

“This is a huge issue for you,” Holbrooke said, looking hard at Karzai. “I urge you to sit down with NATO and the Embassy to work on a quick-reaction administrative effort to bring to the districts health, schools, and, above all, justice.”

Karzai nodded.

The subject of corruption didn’t come up at the lunch, and when he and Karzai met privately, Holbrooke told me, he didn’t explicitly address drug money. On the flight home, I asked Holbrooke how he could turn America’s enormous investment in Afghanistan into leverage. Could he threaten to cut back on aid?

He waved off the idea. “That really hurts Karzai.”

Then what?

Holbrooke paused for a full ten seconds. “Well, it’s a constant tension in relationships like this one between what the Americans want and what the local officials want,” he said. “And we’re not always right about our goals—what we want—and the government we’re supporting is not always right.”

So, I asked Holbrooke, you can’t yell at Karzai and Zardari the way you yelled at Milosevic?

The election on August 20th was a disaster that could change the course of the war. The evidence of fraud by Karzai’s campaign was so overwhelming that it threatened to render the entire vote illegitimate. Publicly, Holbrooke hailed the election; privately, colleagues said, he suggested that a runoff between Karzai and his main challenger, Abdullah Abdullah, might be necessary for the appearance of legitimacy. Karzai got wind of these words, and, when he and Holbrooke met, the Afghan President exploded, accusing the Americans of plotting to drive him out of office. Since then, Holbrooke has maintained a detached public stance, in order not to antagonize America’s partner in Kabul and undermine the Afghan government’s standing. He even compared Afghanistan’s vast state-sponsored vote theft to an electoral controversy in Minnesota, saying, “That happens in democracies, even when they are not in the middle of a war.”

Karzai, with his expressed fears about intimidation and low turnout in Pashtun areas, had been blowing smoke in the Americans’ faces: in those very districts, with few or no voters going to the polls, his associates had been free to stuff empty boxes full of falsified ballots or set up phantom polling sites. The Americans appeared to have been unready for fraud on such a scale—before the election, Holbrooke’s main concerns seemed to be violence and voter apathy. Now there is a strong possibility that a stolen election will leave Karzai in power for five more years, at the very moment that Obama has to answer his generals’ request to send thousands more troops to fight, and perhaps die, on behalf of the Afghan government. But since his speech in late March the President has said very little publicly about the war, almost as if he lacked conviction about his own policy.

Christopher Hill once said of Holbrooke, “He often works on the music before he gets to the words, creating an atmosphere and a sense of what are we dealing with—are we dealing with a sad song, or what? Right now, Richard Holbrooke is getting a sense of the issues, the people. Eventually, the music will shift from Vietnam to the Balkans. And if he gets to a negotiation it will be realistic.” When I repeated Hill’s remark to Holbrooke on the plane, he took out a pen, and on a napkin he wrote down “INSTITUTION BUILDING.” He drew a line under it, and below the line he wrote “DIP PHASE.” “Things are not sequential,” Holbrooke said. “They have to be parallel processes.” He acknowledged that no Dayton would come at the end of the diplomatic phase. In both Vietnam and the Balkans, he said, “there was always a fixed adversary, with whom you could talk even while fighting.” This time, the enemy had no capital, no government. It was very hard to imagine a cast of characters, in suits and uniforms and turbans, seated around a table, preparing to end the Af-Pak war, with Holbrooke standing over them, smiling the smile that told you he had won.

In our conversations, Holbrooke admitted that much of his new job had “a back-to-the-future quality,” but he was wary of the subject of Vietnam, as if he smelled a trap. On the flight home, exasperated with my questions about his earlier life, he wrote out and handed to me a short account of the main reasons for America’s failure in Vietnam, which concluded, “The mission itself was based on a profound misreading, by five presidents and their advisors, of the strategic importance of Vietnam to the U.S.”

Even so, Holbrooke couldn’t stop invoking the war of his youth. From Kabul, he called the journalist Stanley Karnow, an old friend, and put him on the phone with General McChrystal to discuss the lessons of Vietnam. He mentioned Vietnam in staff meetings in Washington, and he brought it up in a speech to American Embassy personnel on my last day in Kabul: “Having been in similar circumstances earlier in my career, in another war—as they say, in a distant galaxy and another time—I know what it’s like to be out here in difficult conditions without your family.” When he called for the Embassy to encourage spouses to come live in Kabul, despite the danger, Holbrooke was unconsciously repeating an idea that he had put forth in a memo in 1966.

On the trip, I watched him avoid the mistakes of his predecessors in Vietnam. He informed himself deeply, asked hard questions, pressed for an exit strategy, and emphasized the need to “Afghanize” the war. Vietnam helped Holbrooke understand the fine details of pacification programs, and made him confront the largest strategic question—whether a war should be fought at all. In Vietnam, what couldn’t be done didn’t need to be done; the war was a folly. Holbrooke was working from the simple deduction that, because Al Qaeda threatened the United States, America did need to be there. Obama had set the policy, and Holbrooke was carrying it out, relentlessly.

Holbrooke must know that there will be no American victory in this war; he can only try to forestall potential disaster. But if he considers success unlikely, or even questions the premise of the war, he has kept it to himself. “Americans cannot think of a situation where, in the face of attacks by Al Qaeda, they would give up, they would say, ‘The hell with it, we have to leave,’ “ he told me. “It’s just not an acceptable course of action.” It was as if, for Holbrooke, the year would always be 1962, his career at its beginning. He said, “I still believe in the possibility of the United States, with all its will and all its strength, and I don’t just mean military, persevering against any challenge. I still believe in that.” ♦